To make this recipe in less time, you can substitute organic canned butternut-squash puree for the fresh squash. For the decorating technique, see our step-by-step photos.

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Ingredients

Ingredient Checklist

Directions

Instructions Checklist
  • Preheat oven to 400 degrees. Cut squash in half lengthwise and scoop out seeds. Place, cut-side down, on a parchment-lined rimmed baking sheet and roast until soft, 45 to 50 minutes.

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  • When squash is cool enough to handle, scoop out flesh and transfer to a food processor; process until smooth. Transfer to a cheesecloth-lined colander set over a bowl. Squeeze out excess moisture and let stand, covered with plastic, at least 2 hours or, refrigerated, up to 3 days. Return to room temperature before using.

  • On a lightly floured piece of parchment, roll out round disk of dough 1/8 inch thick. Transfer to a 9-inch pie dish. Trim dough flush with rim, prick inside all over with a fork, and refrigerate.

  • Roll square disk of dough into an 11-by-14-inch rectangle (between 1/8 and 1/16 inch thick). Freeze until firm but pliable, about 10 minutes. Use a knife or pastry wheel and a ruler to cut fifteen 1/4-inch-wide strips of dough along the short side. (Use an assortment of cookie cutters to cut out decorative shapes for pie top from remaining dough.)

  • Working with 5 strips at a time, gently press tops together to adhere. Place 3 strips to one side and 2 to the other. Make a fish-tail braid by bringing outer-third strip over to the center of side with 2 strips. Repeat, with outer-third strip always moving to middle to join side with 2 strips. Repeat fishtail-braiding with remaining strips of dough, so you have 3 braids of 5 strips each.

  • Beat 1 egg with 1 teaspoon water; brush piecrust rim with egg wash. Place braids over rim, cutting them as needed to fit circumference of pie, and press gently to adhere. Freeze piecrust and decorative cut-outs until firm, about 20 minutes. Brush edge with egg wash.

  • Preheat oven to 400 degrees with racks in lower and upper thirds. Line crust with parchment, keeping it away from decorative rim. Fill with dried beans or pie weights.

  • Bake piecrust on lower rack until edges begin to turn golden and bottom is dry, 22 to 25 minutes. Carefully remove parchment and beans. Reduce oven temperature to 375 degrees and return crust to oven. Place chilled cut-outs on a separate parchment-lined baking sheet and brush with egg wash; place on upper rack. Bake until both piecrust and cutouts are golden brown and dry, 10 to 15 minutes more (smaller cutouts will bake more quickly). Let cool slightly on a wire rack.

  • Reduce oven temperature to 325 degrees. Whisk together 1 cup squash puree and remaining3 eggs. In a separate bowl, whisk together brown sugar, cornstarch, salt, and spices. Whisk dry ingredients into squash mixture, then stir in vanilla and evaporated milk to combine. Pour filling into piecrust; tent rim with foil and bake until center is just set, 50 to 65 minutes. Let cool completely on rack.

  • Dust cutouts with confectioners' sugar and use to decorate top. When ready to slice pie, remove cutouts. Serve, with a few cutouts and a dollop of whipped cream on top of each slice.

Cook's Notes

To transfer dough to the refrigerator or freezer with ease, roll it on parchment, and keep a cookie sheet or an upside-down rimmed baking sheet close at hand -- that way you can just slide the parchment onto it for moving.

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